Trifluoroacetic acid → HCID 86666635, compound

HRID 587849Notes

Reaction equation

HRID 587849 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([C:17](=[O:37])[NH:18][C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:35])([C:31]([F:34])([F:33])[F:32])[C:27]([F:30])([F:29])[F:28])=[CH:21][C:20]=2[Cl:36])[CH:14]=[CH:13][C:3]=1[CH2:4][NH:5]C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:5][CH2:4][C:3]1[CH:13]=[CH:14][C:15]([C:17]([NH:18][C:19]2[C:20]([Cl:36])=[CH:21][C:22]([C:26]([F:35])([C:27]([F:28])([F:29])[F:30])[C:31]([F:32])([F:34])[F:33])=[CH:23][C:24]=2[Cl:25])=[O:37])=[CH:16][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86666636HCID 86666636, compound

Product 1

HCID 86666635HCID 86666635, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (2-chloro-4-{[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-phenyl]carbamoyl}benzyl)carbamate (0.85 g) was dissolved in methylene chloride (15 ml). Trifluoroacetic acid (2 ml) was added to the solution, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off under reduced pressure. The residue was dissolved in methylene chloride (15 ml), and an aqueous solution of potassium carbonate was added to the solution under stirring. The organic phase was separated and the aqueous layer was extracted with methylene chloride and dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product (0.65 g) of 4-(aminomethyl)-3-chloro-N-[2,6-dichloro-4-(1,1,1,2,3,3,3heptafluoro propan-2-yl)-phenyl]benzamide. The crude product was used for the next step without further purification.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride (15 ml)
  3. additionan aqueous solution of potassium carbonate was added to the solution
  4. stirringunder stirring
  5. customThe organic phase was separated
  6. extractionthe aqueous layer was extracted with methylene chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe drying agent was removed by filtration
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-07c02c7836c84d1dbfa11ade25f4c8a1
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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